Ophthalmic lens media insert

ABSTRACT

This invention discloses methods and apparatus for providing an ophthalmic lens with media including an energy receptor. In some embodiments, the media includes an insert placed in a cavity formed to cast mold an ophthalmic lens from a reactive mixture.

RELATED APPLICATIONS

This application is a divisional of U.S. patent application Ser. No.12/405,586 filed on Mar. 17, 2009 which claims priority of U.S. PatentApplication Ser. No. 61/040,772, filed on Mar. 31, 2008.

FIELD OF USE

This invention describes methods and apparatus for the fabrication of anenergized ophthalmic lens and more specifically of an ophthalmic lenswith a media insert including an energy source.

BACKGROUND

Traditionally an ophthalmic device, such as a contact lens, anintraocular lens or a punctal plug included a biocompatible device witha corrective, cosmetic or therapeutic quality. A contact lens, forexample, can provide one or more of: vision correcting functionality;cosmetic enhancement; and therapeutic effects. Each function is providedby a physical characteristic of the lens. A design incorporating arefractive quality into a lens can provide a vision corrective function.A pigment incorporated into the lens can provide a cosmetic enhancement.An active agent incorporated into a lens can provide a therapeuticfunctionality. Such physical characteristics are accomplished withoutthe lens entering into an energized state.

More recently, it has been theorized that active components may beincorporated into a contact lens. Some components can includesemiconductor devices. Some examples have shown semiconductor devicesembedded in a contact lens placed upon animal eyes. However, suchdevices lack a free standing energizing mechanism. Although wires may berun from a lens to a battery to power such semiconductor devices, and ithas been theorized that the devices may be wirelessly powered, nomechanism for such wireless power has been available.

It is desirable therefore to have additional methods and apparatusconducive to the formation of ophthalmic lenses that are wirelesslyenergized to an extent suitable for powering a semiconductor deviceincorporated into a biomedical device, such as an ophthalmic lens.

SUMMARY

Accordingly, the present invention includes methods and apparatus forforming an ophthalmic lens, with an energized portion capable ofpowering an active component. In some embodiments, the ophthalmic lenswill include a cast molded silicone hydrogel with a media insertincluding energy receptor capable of wirelessly receiving energy andpowering an electronic component. The energized portion can be created,for example via a jetting process or a pad printing process or automatedplacement wherein a conductive material is placed on a mediaincorporated into the lens.

Additional embodiments include methods of forming an ophthalmic lenswhich include the steps of depositing a media including an energyreceptor into a mold part for fashioning an ophthalmic lens.

The energy receptor can be deposited onto the media via ink jet, padprint, or mechanical placement. A reactive monomer mix is placed intoone of: the first mold part and the second mold part. The first moldpart is positioned proximate to the second mold part thereby forming alens cavity with the media including the energy receptor and at leastsome of the reactive monomer mix in the lens cavity; and exposing thereactive monomer mix to actinic radiation.

Lenses are formed via the control of actinic radiation to which thereactive monomer mixture is exposed.

DESCRIPTION OF THE DRAWINGS

FIG. 1 illustrates a mold assembly apparatus and media according to someembodiments of the present invention.

FIG. 2A illustrates a top down view of an ophthalmic lens with a mediaincluding a component and energy receptor.

FIG. 2B illustrates a side view of an ophthalmic lens with a mediaincluding a component and energy receptor.

FIG. 3 illustrates an apparatus utilized to place a media with an energyreceptor in a lens mold.

FIG. 4 illustrates method steps according to some embodiments of thepresent invention.

FIG. 5 illustrates method steps according to some additional aspect ofthe present invention.

FIG. 6 illustrates a processor that may be used to implement someembodiments of the present invention.

DETAILED DESCRIPTION OF THE INVENTION

The present invention includes ophthalmic lenses and methods of makingthe ophthalmic lenses. In particular, the present invention includes anophthalmic lens with a wireless energy receptor and informationprocessing component imparted to a lens or lens mold part via mediainsert. In some embodiments, the present invention includes a hydrogelcontact lens including a media comprising a generally annular energyreceptor around a periphery of an optic zone in the contact lens.Additional embodiments can include an energy receptor portion thatincludes a coil or other pattern of conductive material incorporatedinto a media included in an ophthalmic lens. The pattern can be basedupon a tuned wavelength of energy which can be wirelessly transmitted tothe lens.

In some embodiments, a pattern of conductive material can be locatedexterior to an optic zone through which a wearer of a lens would see,while other embodiments can include a pattern of conductive materialwhich is small enough to not adversely affect the sight of a contactlens wearer and therefore can be located within, or exterior to, anoptical zone.

In general, according to some embodiments of the present invention, amedia insert including an energy receptor is embodied within anophthalmic lens. In some embodiments, the energy receptor can bedeposited onto the media via a jet printing process which places thereceptor material in a desired location. The media insert ismechanically placed in position relative to a mold part used to fashionthe lens. In some embodiments, a component is placed in electricalcommunication with the receptor material included on the media such thatthe receptor material can provide electrical power to power thecomponent. Subsequent to placement of the media insert a ReactiveMixture can be shaped by respective mold parts and polymerized to formthe ophthalmic lens.

DEFINITIONS

As used herein, “energy receptor” refers to a medium that functions asan antenna for receiving wireless energy, such as, for example via radiowave transmission.

As used herein, “energy reception portion” refers to a portion of abiomedical device, such as an ophthalmic lens, which is functional as anenergy receptor.

As referred to herein, “ink jet”, refers an apparatus for propellingdroplets of liquid or molten material onto a media. Ink jet apparatuscan include, by way of non-limiting example, one or more of: piezoelectric ink jet apparatus; thermal ink jet and continuous ink jetapparatus.

As referred to herein, the term “ink jetting” or “jetting” refers to anaction resulting in the propulsion of droplets or molten material onto amedia.

As used herein “lens” refers to any ophthalmic device that resides in oron the eye. These devices can provide optical correction or may becosmetic. For example, the term lens can refer to a contact lens,intraocular lens, overlay lens, ocular insert, optical insert or othersimilar device through which vision is corrected or modified, or throughwhich eye physiology is cosmetically enhanced (e.g. iris color) withoutimpeding vision. In some embodiments, the preferred lenses of theinvention are soft contact lenses are made from silicone elastomers orhydrogels, which include but are not limited to silicone hydrogels, andfluorohydrogels.

As used herein, the term “lens forming mixture” or “Reactive Mixture” or“RMM”(reactive monomer mixture) refers to a monomer or prepolymermaterial which can be cured and crosslinked or crosslinked to form anophthalmic lens. Various embodiments can include lens forming mixtureswith one or more additives such as: UV blockers, tints, photoinitiatorsor catalysts, and other additives one might desire in an ophthalmiclenses such as, contact or intraocular lenses.

As used herein “lens forming surface” means a surface that is used tomold a lens. In some embodiments, any such surface 103-104 can have anoptical quality surface finish, which indicates that it is sufficientlysmooth and formed so that a lens surface fashioned by the polymerizationof a lens forming material in contact with the molding surface isoptically acceptable. Further, in some embodiments, the lens formingsurface 103-104 can have a geometry that is necessary to impart to thelens surface the desired optical characteristics, including withoutlimitation, spherical, aspherical and cylinder power, wave frontaberration correction, corneal topography correction and the like aswell as any combinations thereof.

As used herein, the term “media insert” refers to a rigid, semi rigid orflexible platform for supporting an energy receptor.

As used herein, the term “mold” refers to a rigid or semi-rigid objectthat may be used to form lenses from uncured formulations. Somepreferred molds include two mold parts forming a front curve mold partand a back curve mold part.

As used herein, “optical zone” means that area of an ophthalmic lensthrough which a wearer of the ophthalmic lens sees.

As used herein, “released from a mold,” means that a lens is eithercompletely separated from the mold, or is only loosely attached so thatit can be removed with mild agitation or pushed off with a swab.

Molds

Referring now to FIG. 1, a diagram of an exemplary mold 100 for anophthalmic lens is illustrated with an energy receiving portion 109. Asused herein, the terms a mold includes a form 100 having a cavity 105into which a lens forming mixture 110 can be dispensed such that uponreaction or cure of the lens forming mixture, an ophthalmic lens of adesired shape is produced. The molds and mold assemblies 100 of thisinvention are made up of more than one “mold parts” or “mold pieces”101-102. The mold parts 101-102 can be brought together such that acavity 105 is formed between the mold parts 101-102 in which a lens canbe formed. This combination of mold parts 101-102 is preferablytemporary. Upon formation of the lens, the mold parts 101-102 can againbe separated for removal of the lens.

At least one mold part 101-102 has at least a portion of its surface103-104 in contact with the lens forming mixture such that upon reactionor cure of the lens forming mixture 110 that surface 103-104 provides adesired shape and form to the portion of the lens with which it is incontact. The same is true of at least one other mold part 101-102.

Thus, for example, in a preferred embodiment a mold assembly 100 isformed from two parts 101-102, a female concave piece (front piece) 102and a male convex piece (back piece) 101 with a cavity formed betweenthem. The portion of the concave surface 104 which makes contact withlens forming mixture has the curvature of the front curve of anophthalmic lens to be produced in the mold assembly 100 and issufficiently smooth and formed such that the surface of an ophthalmiclens formed by polymerization of the lens forming mixture which is incontact with the concave surface 104 is optically acceptable.

In some embodiments, the front mold piece 102 can also have an annularflange integral with and surrounding circular circumferential edge 108and extends from it in a plane normal to the axis and extending from theflange (not shown).

A lens forming surface can include a surface 103-104 with an opticalquality surface finish, which indicates that it is sufficiently smoothand formed so that a lens surface fashioned by the polymerization of alens forming material in contact with the molding surface is opticallyacceptable. Further, in some embodiments, the lens forming surface103-104 can have a geometry that is necessary to impart to the lenssurface the desired optical characteristics, including withoutlimitation, spherical, aspherical and cylinder power, wave frontaberration correction, corneal topography correction and the like aswell as any combinations thereof.

At 111, a media is illustrated onto which an energy receptor may beplaced, such as, for example, via ink jet or pad printing. The media 111may be any receiving material onto which supports the conductivematerial. In some embodiments, the media 111 can be a clear coat of amaterial which can be incorporated into a lens when the lens is formed.The clear coat can include for example a pigment as described below, amonomer or other biocompatible material. Additional embodiments caninclude a media comprising an insert, which can be either rigid orformable. In some embodiments, a rigid insert may include an opticalzone providing an optical property (such as those utilized for visioncorrection) and a non-optical zone portion. An energy receptor can bedeposited on one or both of the optic zone and non-optic zone of theinsert.

Rigid inserts can include any material compatible with the lens materialand in various embodiments, may include opaque or non-opaque materials.

Various embodiments also include ink jetting an energy receptor onto aninsert prior to placement of the insert into a mold portion used to forma lens. An insert, or other media 111, may also include one or morecomponents which will receive an electrical charge via the energyreceptor 109.

Mold part 101-102 material can include a polyolefin of one or more of:polypropylene, polystyrene, polyethylene, polymethyl methacrylate, andmodified polyolefins.

A preferred alicyclic co-polymer contains two different alicyclicpolymers and is sold by Zeon Chemicals L.P. under the trade name ZEONOR.There are several different grades of ZEONOR. Various grades may haveglass transition temperatures ranging from 105° C. to 160° C. Aspecifically preferred material is ZEONOR 1060R.

Other mold materials that may be combined with one or more additives toform an ophthalmic lens mold include, for example, Zieglar-Nattapolypropylene resins (sometimes referred to as znPP). On exemplaryZieglar-Natta polypropylene resin is available under the name PP 9544MED. PP 9544 MED is a clarified random copolymer for clean molding asper FDA regulation 21 CFR (c)3.2 made available by ExxonMobile ChemicalCompany. PP 9544 MED is a random copolymer (znPP) with ethylene group(hereinafter 9544 MED). Other exemplary Zieglar-Natta polypropyleneresins include: Atofina Polypropylene 3761 and Atofina Polypropylene3620WZ.

Still further, in some embodiments, the molds of the invention maycontain polymers such as polypropylene, polyethylene, polystyrene,polymethyl methacrylate, modified polyolefins containing an alicyclicmoiety in the main chain and cyclic polyolefins. This blend can be usedon either or both mold halves, where it is preferred that this blend isused on the back curve and the front curve consists of the alicyclicco-polymers.

In some preferred methods of making molds 100 according to the presentinvention, injection molding is utilized according to known techniques,however, embodiments can also include molds fashioned by othertechniques including, for example: lathing, diamond turning, or lasercutting.

Typically, lenses are formed on at least one surface of both mold parts101-102. However, in some embodiments, one surface of a lens may beformed from a mold part 101-102 and another surface of a lens can beformed using a lathing method, or other methods.

Lenses

Referring now to FIG. 2A, an ophthalmic lens 201 is illustrated with anenergy receptor 109 and a component 203. As illustrated, the energyreceptor 109 can include a conductive material, such as, for example,carbon fibers; carbon nano-structures, including carbon nano tubes; anda metallic material. Suitable metallic materials can include, forexample, gold, silver and copper. Carbon nanostructures can includesingle walled carbon nanotubes or multiple walled carbon nanotubes.

The energy receptor 109 can be in electrical communication with acomponent 203. The component 203 can include any device which respondsto an electrical charge with a change in state, such as, for example: asemiconductor type chip; a passive electrical device; or an opticaldevice such as a crystal lens. In some specific embodiments, thecomponent 203 includes an electrical storage device, such as, forexample, a capacitor; ultracapacitor; supercapacitor; a battery or otherstorage component. An electrical storage component 203 can include, forexample: a lithium ion battery located in the periphery of an ophthalmiclens outside of the optic zone and be chargeable via one or more ofradio frequency and magnetic inductance into an energy receptordeposited via ink jetting. Other electrical storage device componentsmay also receive an electrical charge via the energy receptor 109.

Other exemplary embodiments can include a component comprising a radiofrequency identification chip (“RFID chip”) chip. The component 203 mayalso include multiple devices or circuitry. In an effort to providesimplicity in this description, the one or more devices will generallybe referred to in the singular, as a component 203.

FIG. 2B further illustrates that an energy receptor 109 can be placed;ink jetted or pad printed in a pattern 109A onto the media 111. Apattern 109A can be used to increase the electrical length of an energyreceptor present in the lens. In addition, a pattern 109A can be tunedto a wireless wavelength to facilitate or control efficient wirelesstransfer of energy.

As illustrated, in some embodiments, the energy receptor portion 109 andthe component 203 is located outside of an optic zone 202, wherein theoptic zone 202 includes that portion of the lens 201 providing line ofsight for a wearer of the lens 201. Other embodiments may include anenergy receptor 109 in the optic zone portion of an ophthalmic lens. Forexample, such embodiments can include a receptor portion 109 ofconductive particles too small to be viewable without aid to the humaneye.

In some embodiments, a preferred lens type can include a lens 201 thatincludes a silicone containing component. A “silicone-containingcomponent” is one that contains at least one [—Si—O—] unit in a monomer,macromer or prepolymer. Preferably, the total Si and attached O arepresent in the silicone-containing component in an amount greater thanabout 20 weight percent, and more preferably greater than 30 weightpercent of the total molecular weight of the silicone-containingcomponent. Useful silicone-containing components preferably comprisepolymerizable functional groups such as acrylate, methacrylate,acrylamide, methacrylamide, vinyl, N-vinyl lactam, N-vinylamide, andstyryl functional groups.

Suitable silicone containing components include compounds of Formula I

where

R¹ is independently selected from monovalent reactive groups, monovalentalkyl groups, or monovalent aryl groups, any of the foregoing which mayfurther comprise functionality selected from hydroxy, amino, oxa,carboxy, alkyl carboxy, alkoxy, amido, carbamate, carbonate, halogen orcombinations thereof; and monovalent siloxane chains comprising 1-100Si—O repeat units which may further comprise functionality selected fromalkyl, hydroxy, amino, oxa, carboxy, alkyl carboxy, alkoxy, amido,carbamate, halogen or combinations thereof;

where b=0 to 500, where it is understood that when b is other than 0, bis a distribution having a mode equal to a stated value;

wherein at least one R¹ comprises a monovalent reactive group, and insome embodiments between one and 3 R¹ comprise monovalent reactivegroups.

As used herein “monovalent reactive groups” are groups that can undergofree radical and/or cationic polymerization. Non-limiting examples offree radical reactive groups include (meth)acrylates, styryls, vinyls,vinyl ethers, C₁₋₆alkyl(meth)acrylates, (meth)acrylamides,C₁₋₆alkyl(meth)acrylamides, N-vinyllactams, N-vinylamides,C₂₋₁₂alkenyls, C₂₋₁₂alkenylphenyls, C₂₋₁₂alkenylnaphthyls,C₂₋₆alkenylphenylC₁₋₆alkyls, O-vinylcarbamates and O-vinylcarbonates.Non-limiting examples of cationic reactive groups include vinyl ethersor epoxide groups and mixtures thereof. In one embodiment the freeradical reactive groups comprises (meth)acrylate, acryloxy,(meth)acrylamide, and mixtures thereof.

Suitable monovalent alkyl and aryl groups include unsubstitutedmonovalent C₁ to C₁₆alkyl groups, C₆-C₁₄ aryl groups, such assubstituted and unsubstituted methyl, ethyl, propyl, butyl,2-hydroxypropyl, propoxypropyl, polyethyleneoxypropyl, combinationsthereof and the like.

In one embodiment b is zero, one R¹ is a monovalent reactive group, andat least 3 R¹ are selected from monovalent alkyl groups having one to 16carbon atoms, and in another embodiment from monovalent alkyl groupshaving one to 6 carbon atoms. Non-limiting examples of siliconecomponents of this embodiment include2-methyl-,2-hydroxy-3-[3-[1,3,3,3-tetramethyl-1-[(trimethylsilyl)oxy]disiloxanyl]propoxy]propylester (“SiGMA”),2-hydroxy-3-methacryloxypropyloxypropyl-tris(trimethylsiloxy)silane,3-methacryloxypropyltris(trimethylsiloxy)silane (“TRIS”),3-methacryloxypropylbis(trimethylsiloxy)methylsilane and3-methacryloxypropylpentamethyl disiloxane.

In another embodiment, b is 2 to 20, 3 to 15 or in some embodiments 3 to10; at least one terminal R¹ comprises a monovalent reactive group andthe remaining R¹ are selected from monovalent alkyl groups having 1 to16 carbon atoms, and in another embodiment from monovalent alkyl groupshaving 1 to 6 carbon atoms. In yet another embodiment, b is 3 to 15, oneterminal R¹ comprises a monovalent reactive group, the other terminal R¹comprises a monovalent alkyl group having 1 to 6 carbon atoms and theremaining R¹ comprise monovalent alkyl group having 1 to 3 carbon atoms.Non-limiting examples of silicone components of this embodiment include(mono-(2-hydroxy-3-methacryloxypropyl)-propyl ether terminatedpolydimethylsiloxane (400-1000 MW)) (“OH-mPDMS”), monomethacryloxypropylterminated mono-n-butyl terminated polydimethylsiloxanes (800-1000 MW),(“mPDMS”).

In another embodiment b is 5 to 400 or from 10 to 300, both terminal R¹comprise monovalent reactive groups and the remaining R¹ areindependently selected from monovalent alkyl groups having 1 to 18carbon atoms which may have ether linkages between carbon atoms and mayfurther comprise halogen.

In one embodiment, where a silicone hydrogel lens is desired, the lensof the present invention will be made from a reactive mixture comprisingat least about 20 and preferably between about 20 and 70% wt siliconecontaining components based on total weight of reactive monomercomponents from which the polymer is made.

In another embodiment, one to four R¹ comprises a vinyl carbonate orcarbamate of the formula:

wherein: Y denotes O—, S— or NH—;

R denotes, hydrogen or methyl; d is 1, 2, 3 or 4; and q is 0 or 1.

The silicone-containing vinyl carbonate or vinyl carbamate monomersspecifically include:1,3-bis[4-(vinyloxycarbonyloxy)but-1-yl]tetramethyl-disiloxane;3-(vinyloxycarbonylthio)propyl-[tris(trimethylsiloxy)silane];3-[tris(trimethylsiloxy)silyl]propyl allyl carbamate;3-[tris(trimethylsiloxy)silyl]propyl vinyl carbamate;trimethylsilylethyl vinyl carbonate; trimethylsilylmethyl vinylcarbonate, and

Where biomedical devices with modulus below about 200 are desired, onlyone R¹ shall comprise a monovalent reactive group and no more than twoof the remaining R¹ groups will comprise monovalent siloxane groups.

Another class of silicone-containing components includes polyurethanemacromers of the following formulae:

(*D*A*D*G)_(a)*D*D*E¹;

E(*D*G*D*A)_(a)*D*G*D*E¹ or;

E(*D*A*D*G)_(a)*D*A*D*E¹  Formulae IV-VI

wherein:

D denotes an alkyl diradical, an alkyl cycloalkyl diradical, acycloalkyl diradical, an aryl diradical or an alkylaryl diradical having6 to 30 carbon atoms,

G denotes an alkyl diradical, a cycloalkyl diradical, an alkylcycloalkyl diradical, an aryl diradical or an alkylaryl diradical having1 to 40 carbon atoms and which may contain ether, thio or amine linkagesin the main chain;

denotes a urethane or ureido linkage;

_(a) is at least 1;

A denotes a divalent polymeric radical of formula:

R¹¹ independently denotes an alkyl or fluoro-substituted alkyl grouphaving 1 to 10 carbon atoms which may contain ether linkages betweencarbon atoms; y is at least 1; and p provides a moiety weight of 400 to10,000; each of E and E¹ independently denotes a polymerizableunsaturated organic radical represented by formula:

wherein: R¹² is hydrogen or methyl; R¹³ is hydrogen, an alkyl radicalhaving 1 to 6 carbon atoms, or a —CO—Y—R¹⁵ radical wherein Y is —O—Y—S—or —NH—; R¹⁴ is a divalent radical having 1 to 12 carbon atoms; Xdenotes —CO— or —OCO—; Z denotes —O— or —NH—; Ar denotes an aromaticradical having 6 to 30 carbon atoms; w is 0 to 6; x is 0 or 1; y is 0 or1; and z is 0 or 1.

A preferred silicone-containing component is a polyurethane macromerrepresented by the following formula:

wherein R¹⁶ is a diradical of a diisocyanate after removal of theisocyanate group, such as the diradical of isophorone diisocyanate.Another suitable silicone containing macromer is compound of formula X(in which x+y is a number in the range of 10 to 30) formed by thereaction of fluoroether, hydroxy-terminated polydimethylsiloxane,isophorone diisocyanate and isocyanatoethylmethacrylate.

Other silicone containing components suitable for use in this inventioninclude macromers containing polysiloxane, polyalkylene ether,diisocyanate, polyfluorinated hydrocarbon, polyfluorinated ether andpolysaccharide groups; polysiloxanes with a polar fluorinated graft orside group having a hydrogen atom attached to a terminaldifluoro-substituted carbon atom; hydrophilic siloxanyl methacrylatescontaining ether and siloxanyl linkanges and crosslinkable monomerscontaining polyether and polysiloxanyl groups. Any of the foregoingpolysiloxanes can also be used as the silicone containing component inthis invention.

Processes

The following method steps are provided as examples of processes thatmay be implemented according to some aspects of the present invention.It should be understood that the order in which the method steps arepresented is not meant to be limiting and other orders may be used toimplement the invention. In addition, not all of the steps are requiredto implement the present invention and additional steps may be includedin various embodiments of the present invention.

Referring now to FIG. 4, a flowchart illustrates exemplary steps thatmay be used to implement the present invention, at 401, a conductivematerial which can act as an energy receptor 109 is applied to a media.The media 111 may or may not also contain one or more of: a component203, battery and capacitor or other energy storage device.

At 402, a reactive monomer mix can be deposited into a mold part101-102.

At 403, the media 111 with the energy receptor 109 can be placed intothe mold part 101-102. In some preferred embodiments, the media 111 isplaced in the mold part 101-102 via mechanical placement. Mechanicalplacement can include, for example, a robot or other automation, such asthose known in the industry to place surface mount components. Humanplacement of a media 111 with an energy receptor 109 is also within thescope of the present invention. Accordingly, any mechanical placementeffective to place a media 111 with an energy receptor 109 within a castmold part such that the polymerization of a Reactive Mixture 110contained by the mold part will include the energy receptor 109 in aresultant ophthalmic lens.

In some embodiments, a binder layer 111 can be applied to a mold part101-102 prior to placement of the energy receptor on the mold part101-102. A binder layer 111 can include, by way of non-limiting example,a pigment or a monomer. The binding layer may be applied for example viaan ink jetting or pad printing process. In some embodiments, a processordevice, 203 may also be placed into the binder 109 in electrical contactwith the ink jetted energy receptor 111.

At 404, the first mold part can be placed proximate to the second moldpart to form a lens forming cavity with at least some of the reactivemonomer mix and the energy receptor in the cavity. At 405, the reactivemonomer mix within the cavity can be polymerized. Polymerization can beaccomplished for example via exposure to one or both of actinicradiation and heat. At 406, the lens is removed from the mold parts.

In some embodiments, a binding layer can include a binding polymer thatis capable of forming an interpenetrating polymer network with a lensmaterial, the need for formation of covalent bonds between the binderand lens material to form a stable lens 110 is eliminated. Stability ofa lens 110 with an energy receptor placed into the binder is provided byentrapment of the energy receptor 109 in the binding polymer and thelens base polymer. The binding polymers of the invention can include,for example, those made from a homopolymer or copolymer, or combinationsthereof, having similar solubility parameters to each other and thebinding polymer has similar solubility parameters to the lens material.Binding polymers may contain functional groups that render the polymersand copolymers of the binding polymer capable of interactions with eachother. The functional groups can include groups of one polymer orcopolymer interact with that of another in a manner that increases thedensity of the interactions helping to inhibit the mobility of and/orentrap the pigment particles. The interactions between the functionalgroups may be polar, dispersive, or of a charge transfer complex nature.The functional groups may be located on the polymer or copolymerbackbones or be pendant from the backbones.

By way of non-limiting example, a monomer, or mixture of monomers, thatform a polymer with a positive charge may be used in conjunction with amonomer or monomers that form a polymer with a negative charge to formthe binding polymer. As a more specific example, methacrylic acid(“MAA”) and 2-hydroxyethylmethacrylate (“HEMA”) may be used to provide aMAA/HEMA copolymer that is then mixed with a HEMA/3-(N,N-dimethyl)propyl acrylamide copolymer to form the binding polymer.

As another example, the binding polymer may be composed ofhydrophobically-modified monomers including, without limitation, amidesand esters of the formula:

CH₃(CH₂)_(x)-L-COCHR═CH₂

wherein L may be —NH or oxygen, x may be a whole number from 2 to 24, Rmay be a C₁ to C₆ alkyl or hydrogen and preferably is methyl orhydrogen. Examples of such amides and esters include, withoutlimitation, lauryl methacrylamide, and hexyl methacrylate. As yetanother example, polymers of aliphatic chain extended carbamates andureas may be used to form the binding polymer.

Binding polymers suitable for a binding layer may also include a randomblock copolymer of HEMA, MAA and lauryl methacrylate (“LMA”), a randomblock copolymer of HEMA and MAA or HEMA and LMA, or a homopolymer ofHEMA. The weight percentages, based on the total weight of the bindingpolymer, of each component in these embodiments is about 93 to about 100weight percent HEMA, about 0 to about 2 weight percent MAA, and about 0to about 5 weight percent LMA.

The molecular weight of the binding polymer can be such that it issomewhat soluble in the lens material and swells in it. The lensmaterial diffuses into the binding polymer and is polymerized and/orcross-linked. However, at the same time, the molecular weight of thebinding polymer cannot be so high as to impact the quality of theprinted image. Preferably, the molecular weight of the binding polymeris about 7,000 to about 100,000, more preferably about 7,000 to about40,000, most preferably about 17,000 to about 35,000 M_(peak) whichcorresponds to the molecular weight of the highest peak in the SECanalyses (=(M_(n)×M_(w))^(1/2))

For purposes of the invention, the molecular weight can be determinedusing a gel permeation chromatograph with a 90° light scattering andrefractive index detectors. Two columns of PW4000 and PW2500, amethanol-water eluent of 75/25 wt/wt adjusted to 50 mM sodium chlorideand a mixture of polyethylene glycol and polyethylene oxide moleculeswith well defined molecular weights ranging from 325,000 to 194 areused.

One ordinarily skilled in the art will recognize that, by using chaintransfer agents in the production of the binding polymer, by using largeamounts of initiator, by using living polymerization, by selection ofappropriate monomer and initiator concentrations, by selection ofamounts and types of solvent, or combinations thereof, the desiredbinding polymer molecular weight may be obtained. Preferably, a chaintransfer agent is used in conjunction with an initiator, or morepreferably with an initiator and one or more solvents to achieve thedesired molecular weight. Alternatively, small amounts of very highmolecular weight binding polymer may be used in conjunction with largeamounts of solvent to maintain a desired viscosity for the bindingpolymer. Preferably, the viscosity of the binding polymer will be about4,000 to about 15,000 centipoise at 23° C.

Chain transfer agents useful in forming the binding polymers used in theinvention have chain transfer constants values of greater than about0.01, preferably greater than about 7, and more preferably greater thanabout 25,000.

Any desirable initiators may be used including, without limitation,ultra-violet, visible light, thermal initiators and the like andcombinations thereof. Preferably, a thermal initiator is used, morepreferably 2,2-azobis isobutyronitrile and 2,2-azobis2-methylbutyronitrile. The amount of initiator used will be about 0.1 toabout 5 weight percent based on the total weight of the formulation.Preferably, 2,2-azobis 2-methylbutyronitrile is used with dodecanethiol.

A binding polymer layer or other media 111 may be made by any convenientpolymerization process including, without limitation, radical chainpolymerization, step polymerization, emulsion polymerization, ionicchain polymerization, ring opening, group transfer polymerization, atomtransfer polymerization, and the like. Preferably, a thermal-initiated,free-radical polymerization is used. Conditions for carrying out thepolymerization are within the knowledge of one ordinarily skilled in theart.

Solvents useful in the production of the binding polymer are mediumboiling solvents having boiling points between about 120 and 230° C.Selection of the solvent to be used will be based on the type of bindingpolymer to be produced and its molecular weight. Suitable solventsinclude, without limitation, diacetone alcohol, cyclohexanone, isopropyllactate, 3-methoxy 1-butanol, 1-ethoxy-2-propanol, and the like.

In some embodiments, a binding polymer layer 111 of the invention may betailored, in terms of expansion factor in water, to the lens materialwith which it will be used. Matching, or substantially matching, theexpansion factor of the binding polymer with that of the cured lensmaterial in packing solution may facilitate the avoidance of developmentof stresses within the lens that result in poor optics and lensparameter shifts. Additionally, the binding polymer can be swellable inthe lens material, permitting swelling of the image printed using thecolorant of the invention. Due to this swelling, the image becomesentrapped within the lens material without any impact on lens comfort.

In some embodiments, colorants may be included in the binding layer.Pigments useful with the binding polymer in the colorants of theinvention are those organic or inorganic pigments suitable for use incontact lenses, or combinations of such pigments. The opacity may becontrolled by varying the concentration of the pigment and opacifyingagent used, with higher amounts yielding greater opacity. Illustrativeorganic pigments include, without limitation, pthalocyanine blue,pthalocyanine green, carbazole violet, vat orange # 1, and the like andcombinations thereof. Examples of useful inorganic pigments include,without limitation, iron oxide black, iron oxide brown, iron oxideyellow, iron oxide red, titanium dioxide, and the like, and combinationsthereof. In addition to these pigments, soluble and non-soluble dyes maybe used including, without limitation, dichlorotriazine and vinylsulfone-based dyes. Useful dyes and pigments are commercially available.

Coating, or wetting, of the pigment particles with binding polymerprovides better dispersion of the pigment particles in the bulk bindingpolymer. The coating may be achieved by use of electrostatic,dispersive, or hydrogen bonding forces to cover the pigment's surface.Preferably, a high shear force is used to disperse the pigment into thebinding polymer. The pigment may be added to the binding polymer bydispensing the polymer and pigment into a suitable mixer, such as arotary shaft mixer and mixing until a homogeneous mixture results,typically for a period of up to about 30 minutes. The mixture may bethen fed into a high shear mill, such as an Eiger mill to disperse thepigment into the binding polymer. Repeated milling is carried out asnecessary to achieve complete dispersion. Generally, milling is carriedout until the pigments are about 0.2 to about 3 microns in size. Millingmay be carried out using any suitable, commercially available deviceincluding, without limitation, a high shear or ball milling device.

In addition to the pigment and binding polymer, in some embodiments, thebinding layer contains one or more solvents that aid in coating of thebinding layer onto the mold part 101-102. It is another discovery of theinvention that, to facilitate a binding layer that does not bleed or runon the mold part 101-102 surface to which it is applied, it isdesirable, and preferred, that the binding layer 101-102 have a surfacetension below about 27 mN/m. This surface tension may be achieved bytreatment of the surface, for example a mold surface, to which thebinding layer will be applied. Surface treatments may be effected bymethods known in the art, such as, but not limited to plasma and coronatreatments. Alternatively, and preferably, the desired surface tensionmay be achieved by the choice of solvents used in the colorant.

Accordingly, exemplary solvents useful in the binding layer includethose solvents that are capable of increasing or decreasing theviscosity of the binding layer and aiding in controlling the surfacetension. Suitable solvents include, without limitation, cyclopentanones,4-methyl-2-pentanone, 1-methoxy-2-propanol, 1-ethoxy-2-propanol,isopropyl lactate and the like and combinations thereof. Preferably,1-ethoxy-2-propanol and isopropyl lactate are used.

In some preferred embodiments, at least three different solvents areused in the binding layer material of the invention. The first two ofthese solvents, both medium boiling point solvents, are used in theproduction of the binding polymer. Although these solvents may bestripped from the binding polymer after its formation, it is preferredthat they are retained. Preferably, the two solvents are1-ethoxy-2-propanol and isopropyl lactate. An additional low boilingsolvent, meaning a solvent the boiling point of which is between about75 and about 120° C., can be used to decrease the viscosity of thecolorant as desired. Suitable low boiling solvents include, withoutlimitation, 2-propanol, 1-methoxy-2-propanol, 1-propanol, and the likeand combinations thereof. Preferably, 1-propanol is used.

The specific amount of solvents used can depend on a number of factors.For example, the amount of solvents used in forming the binding polymerwill depend upon the molecular weight of the binding polymer desired andthe constituents, such as the monomers and copolymers, used in thebinding polymer. The amount of low boiling solvent used will depend uponthe viscosity and surface tension desired for the colorant. Further, ifthe colorant is to be applied to a mold and cured with a lens material,the amount of solvent used will depend upon the lens and mold materialsused and whether the mold material has undergone any surface treatmentto increase its wettability. Determination of the precise amount ofsolvent to be used is within the skill of one ordinarily skilled in theart. Generally, the total weight of the solvents used will be about 40to about 75 weight percent of solvent will be used.

In addition to the solvents, a plasticizer may be and, preferably is,added to the binding layer to reduce cracking during the drying of thebinding layer and to enhance the diffusion and swelling of the bindinglayer by the lens material. The type and amount of plasticizer used willdepend on the molecular weight of the binding polymer used and, forcolorants placed onto molds that are stored prior to use, the shelf-lifestability desired. Useful plasticizers include, without limitation,glycerol, propylene glycol, dipropylene glycol, tripropylene glycol,polyethylene glycol 200, 400, or 600, and the like and combinationsthereof. Preferably, glycerol is used. Amounts of plasticizer usedgenerally will be 0 to about 10 weight percent based on the weight ofthe colorant.

One ordinarily skilled in the art will recognize that additives otherthan those discussed also may be included in the binding layercomposition of the invention. Suitable additives include, withoutlimitation, additives that aid flow and leveling, additives for foamprevention, additives for rheology modification, and the like, andcombinations thereof.

In some embodiments of the present invention, the binding layer becomesembedded in the lens material upon curing of the lens material. Thus,the binding layer may embed closer to the front or back surface of thelens formed depending on the surface of the mold to which the lens thebinding layer 11 is applied. Additionally, one or more layers of bindinglayer 11 may be applied in any order.

Although invention may be used to provide hard or soft contact lensesmade of any known lens material, or material suitable for manufacturingsuch lenses, preferably, the lenses of the invention are soft contactlenses having water contents of about 0 to about 90 percent. Morepreferably, the lenses are made of monomers containing hydroxy groups,carboxyl groups, or both or be made from silicone-containing polymers,such as siloxanes, hydrogels, silicone hydrogels, and combinationsthereof. Material useful for forming the lenses of the invention may bemade by reacting blends of macromers, monomers, and combinations thereofalong with additives such as polymerization initiators. Suitablematerials include, without limitation, silicone hydrogels made fromsilicone macromers and hydrophilic monomers.

Referring now again to FIG. 4, at 403, the media 111 is positioned withthe reactive mixture in between a first mold part and a second mold partwith the media 111 in contact with the reactive mixture 110.

At 404, a first mold part 101 is placed proximate to the second moldpart 102 to form a lens cavity with the Reactive Monomer mix 110 and themedia insert 111 in the lens cavity. At 405, the reactive mixture ispolymerized, such as for example via exposure to one or both of actinicradiation and heat. At 406, an ophthalmic device 201 incorporating theenergy receptor 109 is removed from the mold parts 101-102 used to forman ophthalmic lens 202.

Referring now to FIG. 5 in another aspect of the present invention, acomponent 203 incorporated into an ophthalmic device 201 can be poweredvia wirelessly transmitted energy. At 501, wireless energy istransmitted to an energy receptor included with a media and incorporatedinto an ophthalmic lens, such as an ophthalmic lens. In someembodiments, the energy can be transmitted at a frequency tuned to anenergy receptor 111 included in an ophthalmic lens 201. At 502, energyis received into the energy receptor included in the ophthalmic lens. Insome embodiments, the energy receptor 111 can store the energy as anelectrical charge.

At 503, the energy received is directed into the information component203. The energy can be directed, for example, via electrical circuitrycapable of conducting the electrical charge. At 504 the component 203performs some action on information. The action can include one or moreof: receiving, transmitting, storing and manipulating information.Preferred embodiments will include the information being processed andstored as digital values.

At 505, in some embodiments, information can be transmitted from theprocessing device. Some embodiments can also include the transmission ofinformation based upon the action performed upon the information.

Apparatus

Referring now to FIG. 3, an automation apparatus 310 is illustrated withone or more media handling devices 311. As illustrated, multiple moldparts, each with an associated media 314 can be contained on a pallet313 and presented to an ink jetting nozzle 311. Embodiments, can includea media handling device 311 individually placing energy receptors 109 inrespective media 314, or multiple media handling devices 311simultaneously placing media with energy receptors respective mold parts314.

Referring now to FIG. 6 a controller 600 is illustrated that may be usedin some embodiments of the present invention. The controller 603includes a processor 610, which may include one or more processorcomponents coupled to a communication device 620. In some embodiments, acontroller 600 can be used to transmit energy to the energy receptorplaced in the ophthalmic lens.

The controller can include a one or more processors, coupled to acommunication device configured to communicate energy via acommunication channel. The communication device may be used toelectronically control one or more of: the transfer of energy to theophthalmic lens receptor and the transfer of digital data to and from anophthalmic lens.

The communication device 620 may be used to communicate, for example,with one or more controller apparatus or manufacturing equipmentcomponents, such as for example ink jet printing apparatus for inkjetting conductive material.

The processor 610 is also in communication with a storage device 630.The storage device 630 may comprise any appropriate information storagedevice, including combinations of magnetic storage devices (e.g.,magnetic tape and hard disk drives), optical storage devices, and/orsemiconductor memory devices such as Random Access Memory (RAM) devicesand Read Only Memory (ROM) devices.

The storage device 630 can store a program 616 for controlling theprocessor 610. The processor 610 performs instructions of the program616, and thereby operates in accordance with the present invention. Forexample, the processor 610 may receive information descriptive of mediaplacement, processing device placement, and the like. The storage device630 can also store ophthalmic related data in one or more databases. Thedatabase may include customized energy receptor designs, metrology data,and specific control sequences for ink jetting conductive material toform an energy receptor.

In some embodiments, an ophthalmic lens with a component, such asprocessor device can be matched with a wireless energy source located onthe person in such form factors as jewelry, shirt collar, hat, or into apair of glasses.

CONCLUSION

The present invention, as described above and as further defined by theclaims below, provides methods of processing ophthalmic lenses andapparatus for implementing such methods, as well as ophthalmic lensesformed thereby.

1-11. (canceled)
 12. A method of transmitting data to or from anophthalmic lens comprising an electrically powered component, the methodcomprising the steps of: wirelessly transmitting energy to an energyreceptor portion of the lens; providing sufficient electrical energy tothe component to enable the component to output digital data; andoutputting digital data from the component.
 13. The method of claim 12wherein the ophthalmic lens comprises and intraocular lens.
 14. Themethod of claim 12 wherein the ophthalmic lens comprises a contact lens.15. The method of claim 12 wherein the step of wirelessly transmittingenergy comprises the transmission of radio waves to a tuned antenna inkjetted onto a media comprising the lens.
 16. The method of claim 12wherein the step of wirelessly transmitting energy comprises thetransmission of magnetic power to conductive material ink jetted onto amedia comprising the lens.
 17. The method of claim 12, wherein theophthalmic lens additionally comprises a transmission component and themethod additionally comprises the steps of: providing sufficientelectrical energy to the transmission component to enable the componentto transmit at least a portion of output digital data; and transmittingdigital data from the component beyond the boundaries of the lens.